By swiping Nick Swisher from the White Sox for Wilson Betemit [1]and two dubious pitching prospects, Brian Cashman has given the Yankees a rousing start to what could be a dramatically entertaining off season. Swisher’s power, patience, and versatility are all major assets, giving the Yankees plenty of flexibility along the outfield and at first base. He’s a legitimate defender at first and in the outfield corners, and has enough athletic ability to play a backup role in center field. Given his earlier track record in Oakland, he also figures to raise his batting average significantly from the .219 mark he posted with the White Sox. And he’s only 28 years old, which makes him a virtual toddler in the Yankees’ thirty something lineup. Make no mistake about it, this is a good first move for Cashman and the Yankees.

So what’s next on the winter agenda? Aside from the imminent bidding on CC Sabathia, I’m curious what will happen with Robinson Cano, who might by New York’s most enigmatic player. If the early signs of winter mean anything at all, the Yankees appear to be preparing for life with Cano in 2009. They’ve already given him permission to play winter league ball for at least a month, so that he can continue using the newfound batting stance he discovered late in the regular season. They’ve also made arrangements to have batting coach Kevin Long work with Cano during his winter league stint. And the Yankees have finally hired minor league defensive instructor Mick Kelleher as their first base and infield coach, at least in part because they believe that Kelleher will have a positive influence on Cano the way that Larry Bowa once did. (Let’s just hope that Kelleher has no influence on Cano’s power stroke. In 11 major league seasons with the Cardinals, Astros, Cubs, Angels, and Tigers, Kelleher hit exactly zero home runs.)

But not so fast. The Yankees, despite the warning signs listed above, should listen to several offers for Cano, their starting second baseman who played in a cloud-filled funk for most of the season. Of all the players the Yankees are likely to deal this winter, Cano still has the most trade value, more than Phil Hughes or Ian Kennedy or Hideki Matsui. Cano was supposedly offered to the Padres as part of a package for Jake Peavy, but San Diego turned down that possibility. He might still become the centerpiece to a deal for another starting pitcher (like the Giants’ Matt Cain) or a center fielder (like Carlos Beltran, to borrow from an earlier rumor). With Cano out of the picture, the Yankees could then step up efforts to sign free agent Orlando Hudson, a player with which the Yankee front office is infatuated. Hudson, while five years older than Cano, would represent a significant defensive upsurge over Cano, who may lack the desire and work ethic to achieve his Gold Glove potential. Hudson would also bring some much needed positive energy to a Yankee clubhouse that has become too staid, too corporate, and too damn passive in recent years.

If I were Cashman, I would first dangle Cano to the Dodgers, whose manager (Joe Torre) and third base coach (Bowa) simply adore the player they came to know during their days in New York. The Yankees should find out if the Dodgers would trade Matt Kemp for Cano straight-up. If not, how about Cano and Melky Cabrera for the 24-year-old Kemp? Or perhaps the Yankees could throw in one of their serviceable arms at Triple-A, someone like Big Foot Britton or Chase Wright. Kemp is exactly what the Yankees need: a young, athletic outfielder with power who happens to bat from the right side. The Yankees could then use Kemp in center field for a season, flanked by Johnny Damon in left and Xavier Nady in right, before shifting Kemp to left field in 2010, when top prospect Austin “Ajax” Jackson is projected to be ready for major league service. At the very least, I’ll guarantee that Matt Kemp will turn out much better than the last Kemp they hired in 1983—free agent outfielder Steve Kemp.

Another possibility could involve the Royals, who have become dissatisfied with the progress made by David DeJesus. Although he hasn’t become the star that the Royals once projected him to be, DeJesus did improve his on-base and slugging percentage in 2008 and is better than any of the Yankees’ current center field options. If the Royals are willing to throw in a prospect and/or a backup catcher, the Yankees might receive enough to surrender Cano. As with Kemp, the 29-year-old DeJesus could play center field for a season or two, before Jackson makes the move up from Scranton-Wilkes Barre. And I promise that DeJesus will have more of an impact than Ivan DeJesus did in the mid-1980s.

All things considered, trading Cano might be the Yankees’ best option in trying to upgrade their problematic center field situation this winter. There are no premier center fielders available in this year’s free agent market, although Rocco Baldelli is an intriguing second-tier player. Furthermore, second basemen are a lot easier to find these days than are quality center fielders. Given these realities of the marketplace, the Yankees’ preferred solution might be to trade Cano after all—despite all the hype about him winning a batting title one of these years—and start moving toward a different solution at second base.

At the very least, the Yankees need to consider the possibility of trading Cano. If the offers in return are not promising, then Cano can always stay, forcing Cashman to look in a few other directions for his next deal…

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Every once in awhile, I’ll receive an interesting e-mail from a baseball personality. That happened last month, when former Tiger and Senator Denny McLain (Denny McLain!) sent me a note tinged with a bit of anger. Disclaimers prevent me from quoting directly from the e-mail, but suffice to say that Denny felt I had overstated the one-sided nature of the trade that sent him to the Senators for three players, including Eddie Brinkman, who recently passed away. More specifically, McLain felt I had exaggerated Brinkman’s worth as a player, apparently as a way of embarrassing McLain.

That certainly wasn’t my intent, not at all. I simply thought Brinkman was an underrated player, a dandy shortstop who became an important part of the Tigers in the early 1970s. I felt that Brinkman deserved the praise on his own merits, not as a way of exaggerating the one-sided trade between the Tigers and Senators. I wrote Denny back, explaining my position, but I received no response. Nonetheless, I hope to hear from him again, since it’s always nice to receive notes from former big league stars…

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Speaking of Brinkman, he was part of a long tradition of light-hitting shortstops that played for the Yankees in the 1970s and eighties. When I first started following the team, Gene “The Stick” Michael was the starting shortstop, and that nickname had nothing to do with his hitting. Then came a nonentity like Jim Mason, who eventually gave way to Bucky Dent, who wouldn’t be remembered nearly as favorably without that home run in 1978. The Yankees really didn’t have a good hitting shortstop until they acquired Roy Smalley in 1983. Unfortunately, he couldn’t play a very good shortstop anymore and got caught in the Yankees’ third base-first base sausage grinder of that time. I guess that’s one reason why I appreciate Derek Jeter more than many of his Sabermetric detractors do. Jeter has given the Yankees an offensive presence at the position for the first time since the early 1960s.

Long before Jeter there was Tom Tresh, an underrated former Yankee who died last month at the age of 71. In 1962, Tresh hit 20 home runs, slugged .441, and drew 67 walks while playing mostly at shortstop, where he replaced an injured Tony Kubek. Tresh wasn’t a particularly good defender at the position—he lacked range and made too many errors—but he was passable considering his offensive production. When Kubek returned from back surgery in ‘63, the Yankees returned Tresh to the outfield, where he continued to put up similar offensive numbers for four additional seasons. Oddly, Tresh didn’t play another game at shortstop until 1968. By then, he was on the downhill slide of an injury-shortened career and just one year removed from retirement.

I wonder what would have happened to Tresh if he had stayed healthy and the Yankees had kept him at shortstop all those years. Would he have been the Derek Jeter of the 1960s? Tresh didn’t have the speed of Jeter, but had more power and drew a similar number of walks. He also would have received some scrutiny for his defensive shortcomings, though not the way that Jeter has in this Sabermetric age. Considering the lack of power hitting shortstops in that era, Tresh might have been selected to several All-Star teams. Given his switch-hitting power and his fine performances in three World Series, Tresh might have built up a reasonable case for Hall of Fame induction.

Tresh’s story should serve as a lesson to all of us as to just how difficult it is for players to put themselves on a path to Cooperstown. You have to be fortunate to stay away from injury and you have to be fortunate to receive the opportunity with the right organization. If those circumstances don’t break favorably, the variation in results becomes the difference between a Derek Jeter and a Tom Tresh.